Process for the preparation of the (-)-antipode of (E)-1-cyclohe

Details Process for the preparation of the (-)-antipode of (E)-1-cyclohe Process for the preparation of the (-)-antipode of (E)-1-cyclohe

1986-03-03

1989-02-14

Hollrah, Glennon H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D24908

Patent

active

048047660

ABSTRACT:
A process for the preparation of the (-)-antipode of (E)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ene of the formula ##STR1## which comprises reacting the (E)-isomer of 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-one of the formula ##STR2## with lithium aluminum hydride in the presence of an inert organic diluent and in the presence of a chiral aminoalcohol at a temperature between -70.degree. C. and +50.degree. C. The (-)-antipode is produced in high selectivity, using (-)-N-methyl-ephedrine.

REFERENCES:
patent: 4592772 (1986-06-01), Kraatz et al.
patent: 4607108 (1986-08-01), Feyen et al.
Tanno et al., "Asymmetrical Reduction of Various, etc" Chem Pharm Bull (1983) 837.
Chem. Pharm. Bull., 837 (1983), No. 3, vol. 31 pp. 837-851.
Chemical Abstracts, vol. 94, No. 17, Apr. 27, 1981, Abstract 139814c, p. 767.

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